2-(2-methyl-5-nitrophenyl)isoindoline-1,3-dione | 33238-32-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2-(2-methyl-5-nitrophenyl)isoindoline-1,3-dione
• 英文别名: N-(2-methyl-5-nitrophenyl)phthalimide；N-(2-methyl-5-nitro-phenyl)-phthalimide；N-(2-Methyl-5-nitro-phenyl)-phthalimid；N-(2-Methyl-5-nitrophenyl)-phthalimid；2-(2-methyl-5-nitrophenyl)-1H-isoindole-1,3(2H)-dione；2-(2-methyl-5-nitrophenyl)isoindole-1,3-dione
• CAS: 33238-32-3
• 化学式: C₁₅H₁₀N₂O₄
• mdl: MFCD00411785
• 分子量: 282.255
• InChiKey: GFEUVENJTFIBRE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  83.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2-methyl-5-nitrophenyl)isoindoline-1,3-dione 在 10percent Pd/C 环己烯 作用下， 以 异丙醇 为溶剂， 以70.6%的产率得到N-(5-amino-2-methyl-phenyl)-phthalimide
  参考文献：
  名称：

  Synthesis and Anticonvulsant and Neurotoxic Properties of Substituted N-Phenyl Derivatives of the Phthalimide Pharmacophore

  摘要：

  A series of compounds including 4-amino (1), 3-amino (2), 4-nitro (3), 2-methyl-3-amino (4), 2-methyl-3-nitro (5), 2-methyl-4-amino (6), 2-methyl-4-nitro (7), 2-methyl-5-amino (8), 2-methyl-5-nitro (9), 2-methyl-6-amino (10), 2-methyl-6-nitro (11), 2,6-dimethyl (12), 2-methyl-3-carboxy (13), 2-methoxycarbonyl (14), 2-methyl-4-methoxy (15), 2,4-dimethoxy (16), 2-chloro-4-amino (17), and 2-chloro-4-nitro (18) N-phenyl substituents of phthalimide were evaluated along with N-[3-methyl-(2-pyridinyl)]phthalimide (19), N-(3-amino-2-methylphenyl)succinimide (20), and phenytoin for anticonvulsant and neurotoxic properties. Initial screening in the intraperitoneal tip) maximal electroshock-induced seizure (MES) test and the subcutaneous pentylenetetrazol-induced seizure (scPtz) test in mice led to the selection of 1, 2, 4, 10, 12, 17, and 19 for oral MES evaluation in rats. The resultant ED(50) values for 4, 10, 17, and phenytoin were 8.0, 28.3, 5.7 and 29.8 mg/kg, respectively. In the batrachotoxin affinity assay, IC(50) values for 17 and phenytoin were 0.15 and 0.93 mu M, respectively, and in the recently validated magnesium deficiency-dependent audiogenic seizure test, ED(50) values of 5.2 and 23 mg/kg were obtained for 17 and phenytoin, respectively. Electrophysiology studies on compound 17 point out its ability to (i) potentiate GABA-evoked current responses with a failure to directly activate the GABAA receptor and (ii) to affect, at 100 mu M excitatory non NMDA, but not NMDA, receptors with a 25% block of kainate-evoked response. Electrophysiology measurements on voltage-gated sodium channels in N1E-115 neuroblastoma cells confirm voltage-dependent block of these channels by compound 17. In view of its interaction with multiple ion channels, one would predict that compound 17 might be active in a wide range of seizure models.

  DOI：

  10.1021/jm990068t
• 作为产物：
  描述：

  苯酐 、 2-氨基-4-硝基甲苯 以 甲醇 为溶剂， 反应 4.0h， 以64%的产率得到2-(2-methyl-5-nitrophenyl)isoindoline-1,3-dione
  参考文献：
  名称：

  Synthesis, Molecular Docking, Cytotoxicity and Antioxidant Activity Evaluation of Isoindoline-1,3-dione Derivatives

  摘要：

  已使用各种胺类化合物对异苯并呋喃-1,3-二酮进行官能化，以在无碱条件下获得异吲哚-1,3-二酮衍生物。通过分子对接、细胞毒性（针对HeLa细胞）和抗氧化活性对所有合成的化合物进行生物活性筛选。ABTS和DPPH用于评估抗氧化活性。在合成的异吲哚-1,3-二酮衍生物（3a-k）中，化合物3e表现出最佳的抗氧化活性，并且在与caspase-3蛋白对接时显示出更好的结合能。对合成的化合物针对宫颈癌细胞系（HeLa）的细胞毒性进行了研究，化合物3e显示出比其他异吲哚衍生物更好的活性。

  DOI：

  10.14233/ajchem.2019.22185

文献信息

• Wanag; Veinbergs, Chemische Berichte, 1942, vol. 75, p. 1558,1567
  作者：Wanag、Veinbergs

  DOI：——

  日期：——
• DE126964
  申请人：——

  公开号：——

  公开（公告）日：——
• Targeted Therapeutics
  申请人：MEDIVATION TECHNOLOGIES, INC.

  公开号：US20170119907A1

  公开（公告）日：2017-05-04

  This disclosure describes compositions and methods for delivering and localizing therapeutic agents to therapeutic targets. This disclosure also provides multivalent forms of cationic dyes (“cationic dye multimers”) and methods by which these compounds can be used to treat joint injuries.
• Synthesis, Molecular Docking, Cytotoxicity and Antioxidant Activity Evaluation of Isoindoline-1,3-dione Derivatives
  作者：Palanichamy Santhosh Kumar、Kuruba Bharath Kumar、Asir Obadiah、Suluvoy Jagadish Kumar、Raman Mohanapriya、Arulappan Durairaj、Subramanian Ramanathan、Samuel Vasanthkumar

  DOI：10.14233/ajchem.2019.22185

  日期：2019.10.12

  A variety of amines have been employed to functionalize isobenzofuran-1,3-dione to obtain isoindoline-1,3-dione derivatives in the base free conditions. All the synthesized compounds are screened for their bioactivity through molecular docking, cytotoxicity (against HeLa) and antioxidant activity. ABTS and DPPH are employed to assess the antioxidant activity. Among the synthesized isoindoline-1,3-dione derivatives (3a-k), compound 3e has showed the best antioxidant activity and also exhibited better binding energy when docked with caspase-3 protein. Cytotoxicity of the synthesized compounds was studied against cervical cancer cell line (HeLa) and compound 3e has displayed better activity than other isoindoline derivatives.

  已使用各种胺类化合物对异苯并呋喃-1,3-二酮进行官能化，以在无碱条件下获得异吲哚-1,3-二酮衍生物。通过分子对接、细胞毒性（针对HeLa细胞）和抗氧化活性对所有合成的化合物进行生物活性筛选。ABTS和DPPH用于评估抗氧化活性。在合成的异吲哚-1,3-二酮衍生物（3a-k）中，化合物3e表现出最佳的抗氧化活性，并且在与caspase-3蛋白对接时显示出更好的结合能。对合成的化合物针对宫颈癌细胞系（HeLa）的细胞毒性进行了研究，化合物3e显示出比其他异吲哚衍生物更好的活性。
• Synthesis and Anticonvulsant and Neurotoxic Properties of Substituted <i>N</i>-Phenyl Derivatives of the Phthalimide Pharmacophore
  作者：Joseph Vamecq、Pierre Bac、Christine Herrenknecht、Pierre Maurois、Philippe Delcourt、James P. Stables

  DOI：10.1021/jm990068t

  日期：2000.4.6

  A series of compounds including 4-amino (1), 3-amino (2), 4-nitro (3), 2-methyl-3-amino (4), 2-methyl-3-nitro (5), 2-methyl-4-amino (6), 2-methyl-4-nitro (7), 2-methyl-5-amino (8), 2-methyl-5-nitro (9), 2-methyl-6-amino (10), 2-methyl-6-nitro (11), 2,6-dimethyl (12), 2-methyl-3-carboxy (13), 2-methoxycarbonyl (14), 2-methyl-4-methoxy (15), 2,4-dimethoxy (16), 2-chloro-4-amino (17), and 2-chloro-4-nitro (18) N-phenyl substituents of phthalimide were evaluated along with N-[3-methyl-(2-pyridinyl)]phthalimide (19), N-(3-amino-2-methylphenyl)succinimide (20), and phenytoin for anticonvulsant and neurotoxic properties. Initial screening in the intraperitoneal tip) maximal electroshock-induced seizure (MES) test and the subcutaneous pentylenetetrazol-induced seizure (scPtz) test in mice led to the selection of 1, 2, 4, 10, 12, 17, and 19 for oral MES evaluation in rats. The resultant ED(50) values for 4, 10, 17, and phenytoin were 8.0, 28.3, 5.7 and 29.8 mg/kg, respectively. In the batrachotoxin affinity assay, IC(50) values for 17 and phenytoin were 0.15 and 0.93 mu M, respectively, and in the recently validated magnesium deficiency-dependent audiogenic seizure test, ED(50) values of 5.2 and 23 mg/kg were obtained for 17 and phenytoin, respectively. Electrophysiology studies on compound 17 point out its ability to (i) potentiate GABA-evoked current responses with a failure to directly activate the GABAA receptor and (ii) to affect, at 100 mu M excitatory non NMDA, but not NMDA, receptors with a 25% block of kainate-evoked response. Electrophysiology measurements on voltage-gated sodium channels in N1E-115 neuroblastoma cells confirm voltage-dependent block of these channels by compound 17. In view of its interaction with multiple ion channels, one would predict that compound 17 might be active in a wide range of seizure models.